“Homeless” can mean different things. It could mean “can’t afford a home, can’t keep a job” like the typical assumption, or it could mean “between homes but capable of getting another” or it could mean “has plenty of money but no home base, just sleeps in hotels or camps and can afford food and clothes when needed”.

It’s not a lifestyle I’d want right now, but it doesn’t automatically mean one can’t thrive. Humans were nomadic for millennia before agriculture gave us a reason and the ability to just stay in one spot.